Sodium ethoxide → (1R,2R,3S,5S)-3-(3,4-Dichlorophenyl)-2-(ethoxymethyl)-8-methyl-8-azabicyclo(3.2.1)octane

HRID 1595220Notes

Reaction equation

HRID 1595220 reaction equation
S([C:5]1C=CC(C)=C[CH:6]=1)(O)(=O)=O.[OH:12][CH2:13][C@@H:14]1[C@@H:20]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)[CH2:19][C@H:18]2[N:29]([CH3:30])[C@@H:15]1[CH2:16][CH2:17]2.[O-]CC.[Na+]>C(O)C>[CH2:5]([O:12][CH2:13][C@@H:14]1[C@@H:20]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)[CH2:19][C@H:18]2[N:29]([CH3:30])[C@@H:15]1[CH2:16][CH2:17]2)[CH3:6]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 86583653HCID 86583653, compound

Product 1

HCID 11370864(1R,2R,3S,5S)-3-(3,4-Dichlorophenyl)-2-(ethoxymethyl)-8-methyl-8-azabicyclo(3.2.1)octaneYield 96.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

(1R,2R,3S)-2-hydroxymethyl-3-(3,4-dichlorophenyl)tropane tosylate (2.5 g, 5.5 mmol) was dissolved in anhydrous ethanol (20 ml). Sodium ethoxide in ethanol (2.4 ml, 2.5 M, 6 mmol) was added and the reaction mixture was refluxed for 72 hours. The solvent was evaporated off. The residue was stirred with water and other and extracted three times with other (3×50 ml) and dried over MgSO4. Evaporation of the solvent yields 1.75 g of the title compound. The product was purified by column chromatography on silica using EtOAc:Et3N (99:1). Yield 1.24 g.

Workup

  1. temperaturethe reaction mixture was refluxed for 72 hours
  2. customThe solvent was evaporated off
  3. extractionother and extracted three times with other (3×50 ml)
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-6323234f6bce45a0bce0a2a256cfef55
Source dataset
uspto-grants-2001_09
Patent number
US06288079B1

Reaction notes

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